McKeown began her career in the folk scene. She released her first album, Monday Morning Cold, on her own label, travelling throughout New England while still a student at Brown University in order to promote the record. Although she had begun studying ornithology, she graduated from Brown with a degree in ethnomusicology.
McKeown's music is difficult to categorize in terms of genre; it has touched upon pop, swing, rock, folk, and electronic music, as well as many other genres. McKeown cites The Hitchhiker's Guide to the Galaxy as an influence on her music.
The Philadelphia Weekly recently described McKeown's music, saying:
More singer-songwriters should follow the lead of Erin McKeown, the kooky songbird who's proved both playful and daring throughout her career. With a lilting delivery and chameleonic instrumentation, she even slipped into French for "Coucou," a gem off her unlikely standards album Sing You Sinners.
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